EP 0 802 183 A1 and U.S. Pat. No. 5,780,497 describe substituted indole compounds of the formulae below:
as well as their use as estrogenic agents, including the treatment of bone loss, cardiovascular disease, maladies associated with or resulting from the proliferation or abnormal development of endometrial or endometrial-like tissues, and disease states or syndromes associated with estrogen deficiency.
EP 0 802 184 A1, published Oct. 22, 1997, describes comparable uses for substituted indole compounds of the formulae below.

Analogous indole compounds having the general structures:
are described in U.S. Pat. No. 5,880,137 (Miller et al.).
U.S. Pat. No. 5,811,120 (Gibson, L. L. et al), titled “Solid orally administerable raloxifene hydrochloride pharmaceutical formulation” (Eli Lilly and Company), describes a composition and process for raloxifene hydrochloride tablets including a surfactant being a sorbitan fatty acid ester or a polyoxyethylene sorbitan fatty acid ester, polyvinylpyrrolidone (PVP), and a water soluble diluent which is a polyol or sugar. Raloxifene has low water solubility. The Gibson et al. patented composition claims the inclusion of PVP and a watersoluble diluent to achieve adequate solubility of raloxifene.
U.S. Pat. No. 5,747,510 (Draper) teaches pharmaceutical formulations containing raloxifene in a dose range of from about 55 to about 150 mg. U.S. Pat. No. 5,747,510 (Gibson et al.) provides raloxifene formulations utilizing a surfactant, polyvinylpyrrolidone and a water soluble diluent, particularly those in which the surfactant is a sorbitan fatty acid ester or a polyoxyethylene sorbitan fatty acid ester.
U.S. Pat. Nos. 5,510,358 (Palkowitz) and 5,919,800 (Palkowitz) teach the synthesis and use of Arzoxifene, its analogs and salt forms, with or without combination with estrogen, for the treatment of osteoporosis, post-menopausal syndrome, cardiovascular-related pathological conditions and estrogen-dependent cancer.
U.S. Pat. Nos. 5,332,727 and 5,480,652 describe the use of antioxidants such as ascorbic acid in a solid pharmaceutical composition to stabilize the drug. In the case of NADH and NADPH formulations, the stabilizers added to the formulation include NaHCO3 and PVP in addition to ascorbic acid and are not added to the formulation for an antioxidant effect per se. In the case of ibuprofen, the antioxidant must be in intimate contact with the active drug agent prior to its incorporation into the formulation in order to achieve its protective effect. This effect is only needed in the presence of alkaline carbonates in these effervescent formulations.
WO 96/21656 (Cameron et al.) teaches novel compounds, including CP 336156, and uses for treating or preventing obesity, breast cancer, osteoporosis, endometriosis, cardiovascular disease and prostatic disease.
Sawicka, J. “The influence of excipients and technological process on cholecalciferol stability and its liberation from tablets”, Pharmazie, 46 (1991), H. 7, pp. 519-521 describes the stabilization of cholecalciferol with various antioxidants in the solid state. The best antioxidant system described, however, yielded only 87.6% of the original content after 1 year of storage and the dissolution of the active material was also quite slow. Thus, improvements are required for stabilization of unstable solid drugs.
In light of the prior art, there is still a need to improve the solubility, stability and absorption qualities of poorly soluble pharmaceutical agents.